Two sissy bois Sex Stories for free 2024 – Y2 Stories

We connected online and then met at my cabin.

I rand–across a guy named Bob at SexStories69. I had written several stories about my crossdressing fetish and he replied and said that he enjoyed my stories very much and that he loved crossdressing as well. I contacted him through his email, and I discovered that he lived in a state that adjoins mine, and since I live very near the state line, he was only about 150 miles away. We continued to write sexy emails to each other about crossdressing and sex and eventually he suggested that we might meet in person. I knew the perfect place. My family owns a cabin on 200 acres of land that borders the national forest, and we only use the cabin 6-8 times every year, but I knew that he would never be able to find the place so I proposed that we meet at the local Walmart parking lot, leave his vehicle, and take my car to the cabin. It was a Saturday afternoon when I met him at the parking lot. He looked different from what I expected…much thinner than I am but clean shaven and tall. We said hello awkwardly and I put his bag in the trunk. We had agreed to bring all of our crossdressing clothes, wigs, makeup, and toys with us. When we got to the cabin I showed Bob around and led him to a room so that he could “get ready.” I then took my bags to another room and began to prepare for what I hoped would be a true sexual adventure. I pulled out all of the stops. I had matching pink panties and bra with a dark pink garter belt and stockings. High heeled shoes and a slinky dress with a long blonde wig. When I was through with my makeup, I headed to the living area to wait. It took Bob a lot longer. I was worried that he was getting cold feet and that I might have frightened him with my eagerness. But after about 20 minutes, Bob came in wearing a yellow sundress and a brown wig. He had on bobby sox and flat soled shoes, but he was wearing a long brown wig and with his makeup, he looked far more like a real girl than I did with my more muscular body. He also had in his hand a ruler, a belt, and what looked like a ping-pong paddle. One of the things that I had told him was that I loved being spanked. My eyes widened when i saw the toys and I asked if those were for me. He said “Yes, which would you prefer?” I was already starting to feel a tingle in my boy-clit as I indicated the paddle since it looked like it would do the most damage. “Why don’t we start with you bending over my knees?” Bob said. I wasted no time in pulling up my slinky dress and lying across his knees. He took the paddle and began to spank my ass with enthusiasm. Periodically he would ask if I wanted him to stop, but I was in heaven. I never wanted it to end. He stood me up, unhooked my garters, pulled down my panties and put me back across his knees, and this time he picked up the ruler and began to spank each of my ass cheeks in turn. I knew that my bottom must be turning beet red. Finally, he said that I had been punished enough. It was time to “get to know each other.” I dropped to my knees in front of him, pulled up his sundress, took his beautiful hard girly clit (at least 7 inches) out of his panties, and began to suck him. He tasted delicious. I was fondling his balls while sucking him and he started to moan and I could tell that if I continued, he would cum. So I stopped and suggested that we both get our clothes off. We took off the dress, skirt, and panties but both kept our bras on. This time he took my boi clit in his mouth and began to suck on it. I was really starting to enjoy myself, when Bob brought out tube of lube and asked if I was ready to get fucked. “Yes, please” is all that I could manage to say. He bent me over the couch, lubed up my boi pussy and his cock, and proceeded to ease himself into me. I wanted it all. I wanted every inch of him inside me. Very shortly he was slamming himself against me and I was pushing back against him and starting to feel like a real girl getting myself fucked hard. His legs were getting tired, so he sat down on the couch and I climbed on top of him . My legs were on either side of his knees. I slowly lowered myself onto his hard cock, and began to rock. I was really starting to get turned on again and could feel an orgasm building inside me. As I bounced on Bob’s stiff dick, he bent over, pulled my bra up and began to bite on my nipple. That was it. That put me over the top. I could feel myself spurting, and I looked down and my white sticky cum was going everywhere. When Bob saw me spurting my jizz, it must have triggered him as well. I felt his cock throbbing inside me, and soon I could feel his hot cum inside my ass. There is not a lot more to tell. We rode ATV’s for a while and went skinny dipping in the creek. We basically sucked and fucked the afternoon away. I had him back to the parking lot before 9 P.M., and we both returned to our homes. But I have a feeling that we will be getting together real soon for another exciting afternoon of crossdressing fun.